Method of manufacturing alcohol esters from triglycerides and alcohols using heterogeneous catalysts based on phosphate or an organophosphorous compound of a group 4 metal

a technology of triglyceride and alcohol, which is applied in the field of new alcohol esters, can solve the problems of difficult economic to obtain both ester and glycerin of high purity, liquid hourly space velocity, and high cost of ester purification plants, so as to improve conversion ratio, reduce reaction temperature and contact time, and high ester selectivity

Inactive Publication Date: 2008-10-23
INST FR DU PETROLE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0016]One advantage of the invention using catalysts based on phosphates or phosphonate or diphosphonate type organophosphorous compounds of at least one metal selected from among zirconium, titanium or hafnium is the capacity thereof to catalyse the transesterification of fatty substances with alcohols heavier than methanol. Thus, it is possible to form ethyl, isopropyl or butyl esters, which is of advantage because the pour points of the esters formed with ethyl, isopropyl or butyl alcohols are often lower than those of methyl esters, the gain being sometimes 10° C., which allows more saturated oils to be initially used.
[0017]Another advantage of the invention using a catalyst based on phosphate or phosphonate or diphosphonate type organophosphorous compounds of at least one metal selected from among zirconium, titanium or hafnium is notably that it allows to decrease the reaction temperature and the contact time between the reactants and/or the alcohol/fatty substance ratio in relation to the prior art, while improving the conversion ratio and by maintaining a high ester selectivity.
[0018]Yet another advantage of the inve

Problems solved by technology

In fact, the glycerin obtained is polluted by alkaline salts or alcoholates, so that the glycerin purification plant is almost as costly as the ester manufacturing plant.
However, it is often difficult to economically obtain both an ester and a glycerin of high purity.
However, the liquid hourly space velocity (volume of oil injected/volume of catalyst/hour) is low, the amount of glycerin collected is much less than that theoreticall

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Transesterification of Vegetable Oils (Rapeseed Oil) by Methanol from a Solid Catalyst of Zirconium Phosphate Type Zr(OPO3K)2 at 180° C.

[0083]25 g rapeseed oil, 25 g methanol and 1 g catalyst in powder form are fed into a closed reactor at ambient temperature. The methanol / oil mass ratio is thus 1, which corresponds to a molar ratio of 27.5. The reactor is then closed, stirred (200 rpm) and heated to 180° C. by means of a heating magnetic stirrer. The temperature of the reaction medium is stabilized at 180° C. after 20 minutes heating. The pressure is the autogenous pressure of alcohol at the operating temperature. The reaction is monitored as soon as the temperature of the reaction medium has reached the set temperature value. Samples are regularly taken in order to follow the progress of the reaction. After 6 hours reaction, stirring is stopped and the reactor is left to cool down to ambient temperature. The samples taken and the final effluent are washed by means of a NaCl-satura...

example 2

Transesterification of Vegetable Oils (Rapeseed Oil) by Methanol from a Solid Catalyst of Zirconium Phosphate Zr(OPO_K)2 Type at 170° C.

[0086]Example 1 is repeated using 25 g rapeseed oil, 25 g methanol and 1 g catalyst in powder form. The reaction is carried out at 170° C., the temperature of the reaction medium being stabilized at 170° C. after 20 minutes heating. The table hereafter gives the results obtained.

Samples (in h)0b0.40.61% by massTriglycerides481531in theDiglyceridesc171153organicMonoglyceride91285phaseaVegetable oil26628390methyl estersadetermined by GPCbt = 0 when the reaction medium is at temperaturec% representing the diglycerides and sterols

[0087]Conversion of the triglycerides starts whereas the reaction medium has not reached 170° C. (26% esters at t0). Thermodynamic equilibrium is reached very rapidly (in 60 min approximately). The conversion (estimated in relation to the triglycerides) is 99% at 60 min.

example 3

Transesterification of Vegetable Oils (Rapeseed Oil) by Methanol from a Solid Catalyst of Zirconium Phosphate Type Zr(OPO3K)2 at 160° C.

[0088]Example 1 is repeated using 25 g rapeseed oil, 25 g methanol and 1 g catalyst in powder form. The reaction is carried out at 160° C., the temperature of the reaction medium being stabilized at 160° C. after 20 minutes heating. The table hereafter gives the results obtained.

Samples (in h)0b0.40.61.5% by massTriglycerides472491in theDiglyceridesc181593organicMonoglyceride712115phaseaVegetable oil28497190methyl estersadetermined by GPCbt = 0 when the reaction medium is at temperaturec% representing the diglycerides and sterols

[0089]Thermodynamic equilibrium is reached very rapidly (in 1.5 h approximately). The conversion (estimated in relation to the triglycerides) is 99% in 1.5 h.

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Abstract

A method of manufacturing a composition of alcohol esters of linear monocarboxylic acids with 6 to 26 carbon atoms from a vegetable or animal oil, neutral or acid, virgin or recycled, with monoalcohols having 1 to 18 carbon atoms, in the presence of a phosphate type catalyst or of an organophosphorous compound of a metal selected from the group made up of zirconium, hafnium and titanium, allows to directly produce, in one or more stages, an ester that can be used as fuel and a pure glycerin.

Description

FIELD OF THE INVENTION[0001]The present invention relates to a new method of manufacturing alcohol esters of monocarboxylic acids from fatty substances of vegetable or animal origin.[0002]The mainly desired reaction is a transesterification carried out according to reaction path I below and possibly a coupled esterification and transesterification reaction, esterification being achieved according to path II below.1 triglyceride+3 alcohols→3 fatty substance esters+glycerin  Path I:Fatty acid+alcohol→fatty acid esters+waterFatty acid+glycerin→glyceride+water  Path II:[0003]Fatty substance esters are currently used in many applications as diesel fuels, furnace fuel oils, ecological solvents, base compounds for manufacturing fatty alcohol sulfonates, amides, ester dimers, etc.[0004]In the case of diesel fuel, which is today a major application for fatty substance esters, a certain number of specifications have been established, whose list, limits and methods belong to standard EN 14,214...

Claims

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Application Information

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IPC IPC(8): C10G2/00
CPCC07C67/03C10G2300/1011B01J21/06B01J21/066C11C3/003B01J27/16C07C69/24C07C69/52Y02P30/20
Inventor LECOCQ, VINCENTMAURY, SYLVIEBAZER-BACHI, DELPHINE
Owner INST FR DU PETROLE
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